Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Tokyo 113-0033, Japan.
Org Lett. 2012 Jun 15;14(12):3080-3. doi: 10.1021/ol301129x. Epub 2012 May 30.
FtmPT1 from Aspergillus fumigatus is a fungal indole prenyltransferase (PT) that normally catalyzes the regiospecific prenylation of brevianamide F (cyclo-L-Trp-L-Pro) at the C-2 position of the indole ring with dimethylallyl diphosphate (DMAPP). Interestingly, FtmPT1 exhibited remarkable substrate tolerance and accepted (E)-4-(1H-indol-3-yl)but-3-en-2-one (1) as a substrate to produce an unnatural novel α-prenylindolylbutenone (1a). This is the first demonstration of the prenylation of a nonaromatic carbon of the acceptor substrate by a fungal indole PT.
烟曲霉来源的 FtmPT1 是一种真菌吲哚 prenyltransferase（PT），通常催化 brevianamide F（cyclo-L-Trp-L-Pro）在吲哚环的 C-2 位置与二甲基烯丙基二磷酸（DMAPP）的区域特异性 prenylation。有趣的是，FtmPT1 表现出显著的底物耐受性，并接受（E）-4-（1H-吲哚-3-基）-3-丁烯-2-酮（1）作为底物，生成一种非天然的新型α-prenylindolylbutenone（1a）。这是真菌吲哚 PT 对受体底物的非芳碳进行 prenylation 的首次证明。
